N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]icosa-5,8,11,14-tetraenamide

• ChemBase ID: 125919
• Molecular Formular: C30H42N2O2
• Molecular Mass: 462.66668
• Monoisotopic Mass: 462.32462859
• SMILES: O=C(CCC/C=C/C/C=C/C/C=C/C/C=C/CCCCC)NCCc1c[nH]c2c1cc(O)cc2
• Canonical SMILES: CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)NCCc1c[nH]c2c1cc(O)cc2
• InChI: InChI=1S/C30H42N2O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(34)31-23-22-26-25-32-29-21-20-27(33)24-28(26)29/h6-7,9-10,12-13,15-16,20-21,24-25,32-33H,2-5,8,11,14,17-19,22-23H2,1H3,(H,31,34)
• InChIKey: QJDNHGXNNRLIGA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]icosa-5,8,11,14-tetraenamide
• IUPAC Traditional name: N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]icosa-5,8,11,14-tetraenamide
• Synonyms: N-arachidonoyl-serotonin; Arachidonoyl serotonin; AA-5-HT; N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-(5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenamide; Arachidonoylserotonin

Database IDs

• CAS Number: 187947-37-1
• MDL Number: MFCD02179189
• PubChem SID: 162220263
• PubChem CID: 14420957; 10027372
• CHEMBL: 191534
• Chemspider ID: 8202943
• Wikipedia Title: Arachidonoyl_serotonin

CALCULATED PROPERTIES

• Acid pKa: 9.556519
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): 7.8121967
• LogD (pH = 7.4): 7.8092356
• Log P: 7.8122354
• Molar Refractivity: 149.1079 cm^3
• Polarizability: 56.99765 Å^3
• Polar Surface Area: 65.12 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: yellow oil

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C30H42N2O2

DETAILS

Sigma Aldrich - A7357

Application
Arachidonoylserotonin is a fatty acid amide hydrolase (FAAH) inhibitor and transient receptor potential vanilloid-type I (TRPV1) antagonist. Both FAAH and TRPV1 are targets for chronic pain treatment. Arachidonoylserotonin has been used in a study to determine the involvement of endovanilloids in the cortical plastic changes associated with peripheral nerve injury.
Biochem/physiol Actions
Arachidonoylserotonin is a Fatty Acid Amide Hydrolase (FAAH) Inhibitor and Transient Receptor Potential Vanilloid-Type I (TRPV1) Antagonist. FAAH and TRPV1 are targets for chronic pain treatment. Arachidonylserotonin is a dual target agent and is analgesic in rodents.